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This work describes the investigation of the Diels-Alder reaction of the electron-rich diene trans-1-methoxy-3-trimethylsilyloxy-1,3-butadiene (Danishefsky′s diene) and the non-activated dienophiles 2-cyclopentenone and 2-methyl-2-cyclopentenone with respect to reactivity, regioselectivity and stereoselectivity. An observed double bond isomerization limits the practicability of 2-cyclopentenone as a dienophile in Diels-Alder reactions. 2-Methyl-2cylopentenone could be converted quantitativelydoi:10.3998/ark.5550190.0013.302 fatcat:k6gcm4b5ivbq3csfw2nrdhu5du